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Stereoselective Metal-Free Reaction of Imidazoles with Isothiocyanates Involving Cyanophenylacetylene: A Shortcut to N-(Z-Alkenyl)imidazole-2-carbothioamides

  作者 TROFIMOV BORIS A; ANDRIYANKOVA LUDMILA V; NIKITINA LINA P; BELYAEVA KSENIYA V; MALKINA ANASTASIYA G; AFONIN ANDREI V; USHAKOV IGOR A  
  选自 期刊  SYNLETT;  卷期  2012年-14;  页码  2069-2072  
  关联知识点  
 

[摘要]N-(Z)-(2-Cyano-1-phenylethenyl)imidazole-2-carbothioamides have been synthesized in up to 91% yield by the new reaction between 1-substituted imidazoles and isothiocyanates in the presence of cyanophenylacetylene under catalyst-and solvent-free conditions at room temperature. The reaction proceeds via zwitterion-carbene intermediates which are trapped by isothiocyanates to form the zwitterion with ambident N-S anionic site, which then undergoes stereo- and regioselective migration of the alkenyl moiety.

 
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